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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014384

Secondary Accession Numbers

HMDB14384

Metabolite Identification

Common Name

Oxiconazole

Description

Oxiconazole is only found in individuals that have used or taken this drug. It is an antifungal medication typically administered in a cream or lotion to treat skin infections such as athlete's foot, jock itch and ringworm. [Wikipedia ]Oxiconazole inhibits ergosterol biosynthesis, which is required for cytoplasmic membrane integrity of fungi. It acts to destabilize the fungal cyctochrome P450 51 enzyme (also known as Lanosterol 14-alpha demethylase). This is vital in the cell membrance structure of the fungus. Its inhibition leads to cell lysis. Oxiconazole has also been shown in inhibit DNA synthesis and suppress intracellular concentrations of ATP. Like other imidazole antifungals, Oxiconazole can increase membrane permeability to zinc, augmenting its cytotoxicity.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

5361463
  Mrv0541 02231214322D          

 26 28  0  0  0  0            999 V2000
    5.2224   -0.4285    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.6340    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9036    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8410    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.6340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.8090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534    2.9036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0334    2.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985    2.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784    2.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 22  1  0  0  0  0
  3 21  1  0  0  0  0
  4 26  1  0  0  0  0
  5  7  1  0  0  0  0
  5 16  1  0  0  0  0
  6  9  1  0  0  0  0
  6 14  1  0  0  0  0
  6 17  1  0  0  0  0
  7 10  2  0  0  0  0
  8 17  2  0  0  0  0
  8 20  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  2  0  0  0  0
 14 20  2  0  0  0  0
 15 16  1  0  0  0  0
 15 22  2  0  0  0  0
 15 23  1  0  0  0  0
 18 21  2  0  0  0  0
 19 21  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0014384
     RDKit          3D
Oxiconazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.5576   -2.4369    1.2527 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3210   -1.3596    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148   -1.4303    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -0.5613    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729    0.3770   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    1.3105   -1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771    1.1578   -0.5130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779    0.0277   -0.6481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -0.1246   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.4697   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3929   -2.1764    0.1147 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7282   -2.2585   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3287   -3.0838    0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3762   -3.5087    1.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138   -2.9649    1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6227    1.1033   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247    2.2345   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9081    3.4107   -0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0607    3.5726   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9160    5.0874   -0.2830 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    2.5199    0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7738    1.3262    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145    0.1324    1.7691 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6862    0.4349   -0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1231    1.6212   -2.0555 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6507   -0.4194   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -2.1536    1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0384   -0.6366    0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7594    2.3509   -0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.1435   -2.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -1.4167   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -2.1969   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2007   -1.7273   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3964   -3.3186    0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -3.1551    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550    2.1227   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540    4.2314   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4073    2.6252    1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6865   -0.3909   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 15 11  1  0
 22 16  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
 26 39  1  0
M  END

5361463
  Mrv0541 02231214322D          

 26 28  0  0  0  0            999 V2000
    5.2224   -0.4285    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.6340    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9036    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8410    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.6340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.8090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534    2.9036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0334    2.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985    2.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784    2.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 22  1  0  0  0  0
  3 21  1  0  0  0  0
  4 26  1  0  0  0  0
  5  7  1  0  0  0  0
  5 16  1  0  0  0  0
  6  9  1  0  0  0  0
  6 14  1  0  0  0  0
  6 17  1  0  0  0  0
  7 10  2  0  0  0  0
  8 17  2  0  0  0  0
  8 20  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  2  0  0  0  0
 14 20  2  0  0  0  0
 15 16  1  0  0  0  0
 15 22  2  0  0  0  0
 15 23  1  0  0  0  0
 18 21  2  0  0  0  0
 19 21  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014384

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18-

> <INCHI_KEY>
QRJJEGAJXVEBNE-MOHJPFBDSA-N

> <FORMULA>
C18H13Cl4N3O

> <MOLECULAR_WEIGHT>
429.127

> <EXACT_MASS>
426.981272881

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
40.00972702778972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(E)-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene][(2,4-dichlorophenyl)methoxy]amine

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
5.838766547333333

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.738241434816746

> <JCHEM_POLAR_SURFACE_AREA>
39.41

> <JCHEM_REFRACTIVITY>
105.947

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxiconazole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014384
     RDKit          3D
Oxiconazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.5576   -2.4369    1.2527 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3210   -1.3596    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148   -1.4303    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -0.5613    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729    0.3770   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    1.3105   -1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771    1.1578   -0.5130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779    0.0277   -0.6481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -0.1246   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.4697   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3929   -2.1764    0.1147 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7282   -2.2585   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3287   -3.0838    0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3762   -3.5087    1.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138   -2.9649    1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6227    1.1033   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247    2.2345   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9081    3.4107   -0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0607    3.5726   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9160    5.0874   -0.2830 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    2.5199    0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7738    1.3262    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145    0.1324    1.7691 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6862    0.4349   -0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1231    1.6212   -2.0555 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6507   -0.4194   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -2.1536    1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0384   -0.6366    0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7594    2.3509   -0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.1435   -2.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -1.4167   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -2.1969   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2007   -1.7273   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3964   -3.3186    0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -3.1551    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550    2.1227   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540    4.2314   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4073    2.6252    1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6865   -0.3909   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 15 11  1  0
 22 16  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
 26 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5361463                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       9.748  -0.800   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       5.747   3.050   0.000  0.00  0.00          Cl+0
HETATM    3 Cl   UNK     0      12.416  -5.420   0.000  0.00  0.00          Cl+0
HETATM    4 Cl   UNK     0       3.080  -1.570   0.000  0.00  0.00          Cl+0
HETATM    5  O   UNK     0       9.748   0.740   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      13.750   3.050   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      11.082   1.510   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      12.980   5.420   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      13.750   1.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.416   0.740   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416  -0.800   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082  -1.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.750  -1.570   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.996   3.955   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   0.740   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   1.510   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.504   3.955   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082  -3.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.750  -3.110   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.520   5.420   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.416  -3.880   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.747   1.510   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -0.800   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414   0.740   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.747  -1.570   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -0.800   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   22                                                            
CONECT    3   21                                                            
CONECT    4   26                                                            
CONECT    5    7   16                                                       
CONECT    6    9   14   17                                                  
CONECT    7    5   10                                                       
CONECT    8   17   20                                                       
CONECT    9    6   10                                                       
CONECT   10    7    9   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12    1   11   18                                                  
CONECT   13   11   19                                                       
CONECT   14    6   20                                                       
CONECT   15   16   22   23                                                  
CONECT   16    5   15                                                       
CONECT   17    6    8                                                       
CONECT   18   12   21                                                       
CONECT   19   13   21                                                       
CONECT   20    8   14                                                       
CONECT   21    3   18   19                                                  
CONECT   22    2   15   24                                                  
CONECT   23   15   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   26                                                       
CONECT   26    4   24   25                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0014384
HETATM    1 CL1  UNL     1       6.558  -2.437   1.253  1.00  0.00          CL  
HETATM    2  C1  UNL     1       5.321  -1.360   0.613  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.015  -1.430   1.041  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.061  -0.561   0.512  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.373   0.377  -0.432  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.380   1.311  -1.002  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.077   1.158  -0.513  1.00  0.00           O  
HETATM    8  N1  UNL     1       0.378   0.028  -0.648  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.935  -0.125  -0.352  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.442  -1.470  -0.586  1.00  0.00           C  
HETATM   11  N2  UNL     1      -2.393  -2.176   0.115  1.00  0.00           N  
HETATM   12  C8  UNL     1      -3.728  -2.259  -0.172  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.329  -3.084   0.720  1.00  0.00           C  
HETATM   14  N3  UNL     1      -3.376  -3.509   1.551  1.00  0.00           N  
HETATM   15  C10 UNL     1      -2.214  -2.965   1.189  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.623   1.103  -0.109  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.225   2.235  -0.879  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.908   3.411  -0.924  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.061   3.573  -0.203  1.00  0.00           C  
HETATM   20 CL2  UNL     1      -3.916   5.087  -0.283  1.00  0.00          CL  
HETATM   21  C15 UNL     1      -3.496   2.520   0.559  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.774   1.326   0.590  1.00  0.00           C  
HETATM   23 CL3  UNL     1      -3.314   0.132   1.769  1.00  0.00          CL  
HETATM   24  C17 UNL     1       4.686   0.435  -0.850  1.00  0.00           C  
HETATM   25 CL4  UNL     1       5.123   1.621  -2.055  1.00  0.00          CL  
HETATM   26  C18 UNL     1       5.651  -0.419  -0.338  1.00  0.00           C  
HETATM   27  H1  UNL     1       3.734  -2.154   1.780  1.00  0.00           H  
HETATM   28  H2  UNL     1       2.038  -0.637   0.870  1.00  0.00           H  
HETATM   29  H3  UNL     1       2.759   2.351  -0.874  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.375   1.143  -2.119  1.00  0.00           H  
HETATM   31  H5  UNL     1      -1.742  -1.417  -1.731  1.00  0.00           H  
HETATM   32  H6  UNL     1      -0.545  -2.197  -0.737  1.00  0.00           H  
HETATM   33  H7  UNL     1      -4.201  -1.727  -0.999  1.00  0.00           H  
HETATM   34  H8  UNL     1      -5.396  -3.319   0.710  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.282  -3.155   1.709  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.355   2.123  -1.488  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.554   4.231  -1.525  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.407   2.625   1.137  1.00  0.00           H  
HETATM   39  H13 UNL     1       6.687  -0.391  -0.652  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   26
CONECT    3    4   27
CONECT    4    5    5   28
CONECT    5    6   24
CONECT    6    7   29   30
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   16
CONECT   10   11   31   32
CONECT   11   12   15
CONECT   12   13   13   33
CONECT   13   14   34
CONECT   14   15   15
CONECT   15   35
CONECT   16   17   17   22
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   21
CONECT   21   22   22   38
CONECT   22   23
CONECT   24   25   26   26
CONECT   26   39
END

HMDB0014384
     RDKit          3D
Oxiconazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.5576   -2.4369    1.2527 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3210   -1.3596    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148   -1.4303    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -0.5613    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729    0.3770   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    1.3105   -1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771    1.1578   -0.5130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779    0.0277   -0.6481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -0.1246   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.4697   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3929   -2.1764    0.1147 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7282   -2.2585   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3287   -3.0838    0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3762   -3.5087    1.5508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138   -2.9649    1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6227    1.1033   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247    2.2345   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9081    3.4107   -0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0607    3.5726   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9160    5.0874   -0.2830 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    2.5199    0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7738    1.3262    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145    0.1324    1.7691 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6862    0.4349   -0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1231    1.6212   -2.0555 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6507   -0.4194   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -2.1536    1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0384   -0.6366    0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7594    2.3509   -0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.1435   -2.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -1.4167   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -2.1969   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2007   -1.7273   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3964   -3.3186    0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -3.1551    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550    2.1227   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540    4.2314   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4073    2.6252    1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6865   -0.3909   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 15 11  1  0
 22 16  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
 26 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Oxiconazole nitrate	HMDB

Chemical Formula

C₁₈H₁₃Cl₄N₃O

Average Molecular Weight

429.127

Monoisotopic Molecular Weight

426.981272881

IUPAC Name

(E)-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene][(2,4-dichlorophenyl)methoxy]amine

Traditional Name

oxiconazole

CAS Registry Number

64211-46-7

SMILES

ClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

InChI Identifier

InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18-

InChI Key

QRJJEGAJXVEBNE-MOHJPFBDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

1,3-dichlorobenzene
Aryl chloride
Aryl halide
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014384)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antifungal agent (HMDB: HMDB0014384)
antiinfective agent (HMDB: HMDB0014384)

Biological role

antifungal agent (HMDB: HMDB0014384)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0019 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0019 g/L	ALOGPS
logP	5.28	ALOGPS
logP	5.84	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	6.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.41 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	105.95 m³·mol⁻¹	ChemAxon
Polarizability	40.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	192.68	30932474
DeepCCS	[M-H]-	190.322	30932474
DeepCCS	[M-2H]-	223.77	30932474
DeepCCS	[M+Na]+	198.998	30932474
AllCCS	[M+H]+	188.3	32859911
AllCCS	[M+H-H2O]+	185.8	32859911
AllCCS	[M+NH4]+	190.7	32859911
AllCCS	[M+Na]+	191.4	32859911
AllCCS	[M-H]-	172.2	32859911
AllCCS	[M+Na-2H]-	171.3	32859911
AllCCS	[M+HCOO]-	170.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxiconazole	ClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1	4276.5	Standard polar	33892256
Oxiconazole	ClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1	3000.8	Standard non polar	33892256
Oxiconazole	ClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1	3048.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxiconazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9615000000-f8d5fa55f90a3c0274d3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxiconazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxiconazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 10V, Positive-QTOF	splash10-004i-0040900000-2244e5a8bc8f622118d5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 20V, Positive-QTOF	splash10-000i-0390400000-e9f8c81da4249531df53	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 40V, Positive-QTOF	splash10-00xr-3920000000-2b8888d5586d800c98d9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 10V, Negative-QTOF	splash10-004i-0000900000-7ac95b33d5747267c8a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 20V, Negative-QTOF	splash10-0kdi-2691800000-c74d8b876a02007abf05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 40V, Negative-QTOF	splash10-060u-4930000000-773675c2f231353648b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 10V, Negative-QTOF	splash10-0059-5010900000-d5310ae0910fe9a240a5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 20V, Negative-QTOF	splash10-001i-9020000000-a94bd8e0395e9db7e52a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 40V, Negative-QTOF	splash10-014i-9000000000-272c746157cbf8570345	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 10V, Positive-QTOF	splash10-004i-0000900000-4d57962ed63ea0d13a11	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 20V, Positive-QTOF	splash10-004i-0220900000-223705cb6ad47e786d5e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxiconazole 40V, Positive-QTOF	splash10-0aor-4931000000-07805722b64eb1134557	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00239	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00239	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4514745

KEGG Compound ID

C08075

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxiconazole

METLIN ID

Not Available

PubChem Compound

5361463

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. [PubMed:3069196 ]
Matsui H, Sakanashi Y, Oyama TM, Oyama Y, Yokota S, Ishida S, Okano Y, Oyama TB, Nishimura Y: Imidazole antifungals, but not triazole antifungals, increase membrane Zn2+ permeability in rat thymocytes Possible contribution to their cytotoxicity. Toxicology. 2008 Jun 27;248(2-3):142-50. doi: 10.1016/j.tox.2008.03.022. Epub 2008 Apr 7. [PubMed:18468760 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P: Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. Epub 2007 Nov 12. [PubMed:17998298 ]

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Mahajan MK, Uttamsingh V, Daniels JS, Gan LS, LeDuc BW, Williams DA: In vitro metabolism of oxymetazoline: evidence for bioactivation to a reactive metabolite. Drug Metab Dispos. 2011 Apr;39(4):693-702. doi: 10.1124/dmd.110.036004. Epub 2010 Dec 21. [PubMed:21177487 ]

Showing metabocard for Oxiconazole (HMDB0014384)

MOL for HMDB0014384 (Oxiconazole)

3D MOL for HMDB0014384 (Oxiconazole)

3D SDF for HMDB0014384 (Oxiconazole)

3D-SDF for HMDB0014384 (Oxiconazole)

PDB for HMDB0014384 (Oxiconazole)

3D PDB for HMDB0014384 (Oxiconazole)

SMILES for HMDB0014384 (Oxiconazole)

INCHI for HMDB0014384 (Oxiconazole)

Structure for HMDB0014384 (Oxiconazole)

3D Structure for HMDB0014384 (Oxiconazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References